I think you will be very pleasantly surprised, once I got my first Android phone I TRIED going back to my TP2, numerous times did I try. I would activate it, and by the end of the day I was frustrated and wanted my Hero or Moment back ASAP.
Dialer Skins, as far as the Hero, yes. I know you can make your own, I haven't had time to go into theming yet, but I don't assume it is too hard. Probably just a matter of reading a lot and some trial and error
Second one is a no, you can get apps a lot of places. They install much like winmo apps, put them on SD Card, I have a folder I create called My Apps and just install the APK from there, you may need to be rooted for some apps though.
I feel it is, even more so IMO. It is different customizing it, but I feel it is.
I think you will be very happy. I will give you an XDA link, just PM me, with a VERY easy way to root, and also County has a great Tips thread in the Hero section. I would recommend after you root and everything, partition your SD Card so you can install apps to it and you will be good to go! If you have any questions throw them in there